title: Synthesis of an adenine nucleoside containing the (8'R) epimeric carbohydrate core of amipurimycin and its biological study.
abstract: The (8'R) epimeric carbohydrate core 2 of amipurimycin was synthesized from D-glucose derived allylic alcohol 3 in 11 steps and 13% overall yield. The key steps involve an acid-catalyzed acetonide ring opening of 9 with concomitant formation of an unprecedented pyranose ring skeleton to give 2,7-dioxabicyclo[3.2.1]octane 10. The α-orientation of the furan ring in 10 readily allows the stereoselective β-glycosylation and opening of the furanose ring that on removal of protecting groups affords the pyranosyl adenine nucleoside 2. The antifungal and anticancer activities of 2 were studied.
authors.affiliation: Department of Chemistry, Garware Research Centre, University of Pune, Pune 411 007, India.
authors.forename: Rajendra S
authors.initials: RS
authors.lastname: Mane
authors.forename: Sougata
authors.initials: S
authors.lastname: Ghosh
authors.forename: Balu A
authors.initials: BA
authors.lastname: Chopade
authors.forename: Oliver
authors.initials: O
authors.lastname: Reiser
authors.forename: Dilip D
authors.initials: DD
authors.lastname: Dhavale
mesh_terms: D000143:Acids / Q000737:chemistry; D000225:Adenine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000494:pharmacology; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D002277:Carcinoma / Q000188:drug therapy; D002384:Catalysis; D049109:Cell Proliferation / Q000187:drug effects; D005260:Female; D005658:Fungi / Q000187:drug effects / Q000254:growth & development; D005947:Glucose / Q000737:chemistry; D006031:Glycosylation; D006367:HeLa Cells; D006801:Humans; D009761:Nystatin / Q000494:pharmacology; D009795:Octanes / Q000737:chemistry; D011687:Purines / Q000737:chemistry; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D002583:Uterine Cervical Neoplasms / Q000188:drug therapy
chemical_list: D000143:Acids; D000935:Antifungal Agents; D000970:Antineoplastic Agents; D009795:Octanes; D011687:Purines; D009761:Nystatin; C013810:amipurimycin; D005947:Glucose; D000225:Adenine